There is an increasing need for the preparation of organic compounds as single enantiomers or diastereomers. This is an outgrowth of the requirement for pharmaceuticals to be single chiral entities. Thus the development of new methods for the preparation of enantiomerically pure compounds is important. This proposal describes strategies for obtaining high levels of rho and beta diastereoselectivity in radical reactions with acyclic systems. The proposed work focuses on understanding the factors responsible for selectivity in radical reactions such that future development of new synthetic strategies based on radical intermediates will be feasible. The study also addresses the issues of chiral catalysis in radical reactions, a methodology not available to the synthetic chemist at the present time. The goals of this proposal are: * The development of new strategies for obtaining high levels of acyclic diastereoselection in radical reactions. * The extension of these studies for the introduction of multiple chiral centers using radical methodologies. * The development of radical processes for the synthesis of acetate aldols, aldols, and beta-amino acids. * The development of enantioselective radical reactions using chiral Lewis acids. * The development of radical methods for carbon-carbon bond construction which are inaccessible by ionic methods.